Halogen–Arene Interactions Assist in Self-Assembly of Dyes

Authors

  • Ulrich Mayerhöffer,

    1. Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074 Würzburg (Germany)
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  • Prof. Dr. Frank Würthner

    Corresponding author
    1. Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074 Würzburg (Germany)
    • Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074 Würzburg (Germany)
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  • U.M. thanks the Fonds der Chemischen Industrie for a PhD scholarship.

Abstract

original image

The “dye” is cast: An isodesmic self-assembly process of near-infared-absorbing, acceptor-substituted squaraine dyes, assisted by halogen–halogen and halogen–arene interactions, is observed in toluene. The aggregation process was monitored by UV/Vis/NIR absorption and NMR experiments, thus providing insight into the structural features (see figure; O red, I violet, N blue) as well as the binding strengths of the formed aggregates.

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